HU227562B1 - Derivatives of 2-fluoro-3-de[(2,6-dideoxy-3-c-methyl-3-o-methyl-alpha-l-ribohexopyranosyl)-oxy]-6-o-methyl-3-oxo-erythromycin, and their preparation process - Google Patents
Derivatives of 2-fluoro-3-de[(2,6-dideoxy-3-c-methyl-3-o-methyl-alpha-l-ribohexopyranosyl)-oxy]-6-o-methyl-3-oxo-erythromycin, and their preparation process Download PDFInfo
- Publication number
- HU227562B1 HU227562B1 HU9900958A HUP9900958A HU227562B1 HU 227562 B1 HU227562 B1 HU 227562B1 HU 9900958 A HU9900958 A HU 9900958A HU P9900958 A HUP9900958 A HU P9900958A HU 227562 B1 HU227562 B1 HU 227562B1
- Authority
- HU
- Hungary
- Prior art keywords
- methyl
- formula
- compounds
- compound
- oxo
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 8
- 229960003276 erythromycin Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000012025 fluorinating agent Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- PZFFSGZBQUSNGT-UHFFFAOYSA-N 4-(4-pyridin-3-ylimidazol-1-yl)butan-1-amine Chemical compound NCCCCN1C=NC(C=2C=NC=CC=2)=C1 PZFFSGZBQUSNGT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- ZIPYLWXIFHOMFP-UHFFFAOYSA-N C(=O)=CC=1NC=CC1C Chemical compound C(=O)=CC=1NC=CC1C ZIPYLWXIFHOMFP-UHFFFAOYSA-N 0.000 description 1
- 101100119767 Caenorhabditis elegans fat-4 gene Proteins 0.000 description 1
- 101100468762 Caenorhabditis elegans ric-3 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- JOTXKOXGEZBEEM-UHFFFAOYSA-N azanium;dichloromethane;hydroxide Chemical compound [NH4+].[OH-].ClCCl JOTXKOXGEZBEEM-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical class O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- -1 αethoxy Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9804366A FR2777282B1 (fr) | 1998-04-08 | 1998-04-08 | Nouveaux derives de la 2-fluoro 3-de((2,6-dideoxy 3-c-methyl 3-0-methyl-alpha-l-ribohexopyranosyl) oxyl) 6-o-methyl 3-oxo erythromycine, leur procede de preparation et leur application a la synthese de principes actifs de medicaments |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| HU9900958D0 HU9900958D0 (en) | 1999-06-28 |
| HUP9900958A1 HUP9900958A1 (hu) | 1999-11-29 |
| HUP9900958A3 HUP9900958A3 (en) | 2000-04-28 |
| HU227562B1 true HU227562B1 (en) | 2011-08-29 |
Family
ID=9524992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9900958A HU227562B1 (en) | 1998-04-08 | 1999-04-07 | Derivatives of 2-fluoro-3-de[(2,6-dideoxy-3-c-methyl-3-o-methyl-alpha-l-ribohexopyranosyl)-oxy]-6-o-methyl-3-oxo-erythromycin, and their preparation process |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6121432A (ko) |
| EP (1) | EP0949268B1 (ko) |
| JP (1) | JP4707785B2 (ko) |
| KR (1) | KR100633835B1 (ko) |
| CN (1) | CN1130370C (ko) |
| AT (1) | ATE256139T1 (ko) |
| DE (1) | DE69913413T2 (ko) |
| DK (1) | DK0949268T3 (ko) |
| ES (1) | ES2210999T3 (ko) |
| FR (1) | FR2777282B1 (ko) |
| HU (1) | HU227562B1 (ko) |
| PT (1) | PT949268E (ko) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0105190A3 (en) | 1999-01-27 | 2003-03-28 | Pfizer Prod Inc | Ketolide antibiotics, medicaments containing them and their use |
| US6451768B1 (en) | 1999-04-16 | 2002-09-17 | Kosan Biosciences, Inc. | Macrolide antiinfective agents |
| US6514944B2 (en) | 1999-04-16 | 2003-02-04 | Kosan Biosciences, Inc. | Macrolide antiinfective agents |
| US6939861B2 (en) | 1999-04-16 | 2005-09-06 | Kosan Biosciences, Inc. | Amido macrolides |
| US6458771B1 (en) | 1999-04-16 | 2002-10-01 | Ortho-Mcneil Pharmaceutical, Inc. | Ketolide antibacterials |
| US6590083B1 (en) | 1999-04-16 | 2003-07-08 | Ortho-Mcneil Pharmaceutical, Inc. | Ketolide antibacterials |
| ATE340183T1 (de) | 1999-04-16 | 2006-10-15 | Kosan Biosciences Inc | Antiinfektiöse makrolidderivate |
| CN1351608A (zh) * | 1999-05-24 | 2002-05-29 | 辉瑞产品公司 | 13－甲基红霉素衍生物 |
| JP2001261694A (ja) | 2000-03-06 | 2001-09-26 | Pfizer Prod Inc | ケトライド抗生物質 |
| EP1167376B1 (en) | 2000-06-30 | 2004-07-14 | Pfizer Products Inc. | Macrolide antibiotics |
| US7601695B2 (en) | 2003-03-10 | 2009-10-13 | Optimer Pharmaceuticals, Inc. | Antibacterial agents |
| CN101917850B (zh) * | 2007-10-25 | 2016-01-13 | 森普拉制药公司 | 大环内酯类抗菌剂的制备方法 |
| ES2565083T3 (es) | 2008-10-24 | 2016-03-31 | Cempra Pharmaceuticals, Inc. | Biodefensas usando macrólidos que contienen triazol |
| US9937194B1 (en) | 2009-06-12 | 2018-04-10 | Cempra Pharmaceuticals, Inc. | Compounds and methods for treating inflammatory diseases |
| CN108310000A (zh) | 2009-09-10 | 2018-07-24 | 森普拉制药公司 | 治疗疟疾、结核病和mac疾病的方法 |
| CN103080122A (zh) | 2010-03-22 | 2013-05-01 | 森普拉制药公司 | 大环内脂的结晶形式及其用途 |
| RU2608390C2 (ru) | 2010-05-20 | 2017-01-18 | Семпра Фармасьютикалз, Инк. | Способы получения макролидов и кетолидов, и промежуточных соединений для их получения |
| KR20130120458A (ko) | 2010-09-10 | 2013-11-04 | 셈프라 파마슈티컬스, 인크. | 질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드 |
| EP3216798A3 (en) * | 2010-12-09 | 2017-10-25 | Wockhardt Limited | Ketolide compounds |
| KR20140139083A (ko) | 2012-03-27 | 2014-12-04 | 셈프라 파마슈티컬스, 인크. | 마크롤라이드계 항생제를 투여하기 위한 비경구 제제 |
| JP6426696B2 (ja) | 2013-03-14 | 2018-11-21 | センプラ ファーマシューティカルズ，インコーポレイテッド | 呼吸器疾患の治療のための方法および製剤 |
| AU2014233240B2 (en) | 2013-03-15 | 2018-08-09 | Cempra Pharmaceuticals, Inc. | Convergent processes for preparing macrolide antibacterial agents |
| CN106518939B (zh) * | 2015-09-14 | 2019-12-31 | 江苏奥赛康药业有限公司 | 一种制备Solithromycin化合物的方法 |
| CN106554381A (zh) * | 2015-09-25 | 2017-04-05 | 苏州鹏旭医药科技有限公司 | 酮内酯类抗生素中间体及其制备方法和应用 |
| EP3190122A1 (en) | 2016-01-08 | 2017-07-12 | LEK Pharmaceuticals d.d. | A novel synthetic pathway towards solithromycin and purification thereof |
| CN106432383A (zh) * | 2016-09-14 | 2017-02-22 | 重庆两江药物研发中心有限公司 | 索利霉素及其中间体的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4742049A (en) * | 1986-06-04 | 1988-05-03 | Abbott Laboratories | Semisynthetic erythromycin antibiotics |
| US4740502A (en) * | 1986-06-20 | 1988-04-26 | Abbott Laboratories | Semisynthetic erythromycin antibiotics |
| IL114589A (en) * | 1990-11-21 | 1999-12-22 | Roussel Uclaf | Intermediates for the preparation of the history of erythromycin |
| US5523399A (en) * | 1991-12-27 | 1996-06-04 | Taisho Pharmaceutical Co., Ltd. | 5-O-desosaminylerythronolide derivatives |
| ATE145212T1 (de) * | 1992-04-22 | 1996-11-15 | Taisho Pharmaceutical Co Ltd | 5-0-desosaminylerythronolide a derivate |
| US5527780A (en) * | 1992-11-05 | 1996-06-18 | Roussel Uclaf | Erythromycin derivatives |
| FR2739620B1 (fr) * | 1995-10-09 | 1997-12-19 | Roussel Uclaf | Nouveaux derives de la 5-0-desosaminyl 6-o-methyl erythronolide a, leur procede de preparation et leur application a la preparation de produits biologiquement actifs |
| FR2742757B1 (fr) * | 1995-12-22 | 1998-01-30 | Roussel Uclaf | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| FR2771008B1 (fr) * | 1997-11-17 | 2000-04-28 | Hoechst Marion Roussel Inc | Utilisation des ketolides pour la preparation de compositions pharmaceutiques destinees a prevenir les complications thrombotiques arterielles liees a l'atherosclerose |
-
1998
- 1998-04-08 FR FR9804366A patent/FR2777282B1/fr not_active Expired - Lifetime
-
1999
- 1999-03-22 US US09/273,846 patent/US6121432A/en not_active Expired - Lifetime
- 1999-03-30 JP JP08858099A patent/JP4707785B2/ja not_active Expired - Lifetime
- 1999-04-07 DK DK99400843T patent/DK0949268T3/da active
- 1999-04-07 PT PT99400843T patent/PT949268E/pt unknown
- 1999-04-07 AT AT99400843T patent/ATE256139T1/de active
- 1999-04-07 EP EP99400843A patent/EP0949268B1/fr not_active Expired - Lifetime
- 1999-04-07 ES ES99400843T patent/ES2210999T3/es not_active Expired - Lifetime
- 1999-04-07 CN CN99104863A patent/CN1130370C/zh not_active Expired - Lifetime
- 1999-04-07 DE DE69913413T patent/DE69913413T2/de not_active Expired - Lifetime
- 1999-04-07 KR KR1019990011936A patent/KR100633835B1/ko not_active IP Right Cessation
- 1999-04-07 HU HU9900958A patent/HU227562B1/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU9900958D0 (en) | 1999-06-28 |
| EP0949268A1 (fr) | 1999-10-13 |
| KR19990082977A (ko) | 1999-11-25 |
| EP0949268B1 (fr) | 2003-12-10 |
| ATE256139T1 (de) | 2003-12-15 |
| ES2210999T3 (es) | 2004-07-01 |
| DE69913413D1 (de) | 2004-01-22 |
| HUP9900958A3 (en) | 2000-04-28 |
| CN1130370C (zh) | 2003-12-10 |
| FR2777282B1 (fr) | 2001-04-20 |
| DE69913413T2 (de) | 2004-12-02 |
| FR2777282A1 (fr) | 1999-10-15 |
| KR100633835B1 (ko) | 2006-10-13 |
| US6121432A (en) | 2000-09-19 |
| DK0949268T3 (da) | 2004-03-29 |
| HUP9900958A1 (hu) | 1999-11-29 |
| CN1235162A (zh) | 1999-11-17 |
| JP4707785B2 (ja) | 2011-06-22 |
| JPH11310591A (ja) | 1999-11-09 |
| PT949268E (pt) | 2004-04-30 |
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